Four-and-Twenty was bred and raced by the Alberta Ranches, Ltd. partnership of Max Bell, Frank McMahon and superstar jockey Johnny Longden and his son, Vance.
In his three-year-old season in 1961, the colt won California's most important race for his age group, the one and one-eighth-mile Santa Anita Derby.
He was then sent to Churchill Downs in Louisville, Kentucky where he suffered the first loss of his career when he finished second to Crozier in the Derby Trial Stakes.
In the race, Four-and-Twenty moved into the lead as the field headed for the homestretch but found the extra one-eighth of a mile too much and quickly faded in midstretch.
He returned to racing at age five, winning the Tropicana Hotel of Las Vegas Handicap at Bay Meadows Racetrack in San Mateo, California.